How to Style Chelsea Boots (for Women)

Co-authored by Katie Quinn and Amber Crain

Last Updated: October 15, 2020 References

Chelsea boots are known for their versatility and can easily complement dressy and casual looks. Pair your boots with skinny jeans, a graphic T-shirt, and a leather jacket for an edgy, street-ready look. For a boho-inspired outfit, wear your Chelsea boots with a knee-length vintage dress. If you want to wear your boots to work, go with loose-fit, cropped dress trousers and a long-sleeved blouse. Top off this office-ready ensemble with a matching slim-cut blazer or chunky knit scarf!

Method 1

Method 1 of 2:

Building Casual Outfits

1
Pair skinny jeans with Chelsea boots for a cool, street-wear style. Slim-fit and skinny jeans look great with Chelsea boots, especially if you cuff them once or twice to really show off the shoe. This look is incredibly versatile, so your options are almost limitless when it comes to color combinations and tops!^{[1]
X
Research source}
- For an edgy vibe, wear black leather Chelsea boots with distressed black skinny jeans and a graphic T-shirt. If the weather is chilly, throw on a matching long-sleeved flannel and leave the shirt fully unbuttoned.
- Take the edgy vibe up a notch by pairing black leather Chelsea's with slim-fit pin-striped trousers and a black leather jacket.
- You can also wear light wash skinny jeans to create a more laidback vibe.
2
Wear Chelsea boots with a vintage dress for a boho-inspired look. Go with a floral or paisley patterned dress in a vintage cut. Choose something that falls to about knee-length to really show off your shoes. If weather permits, you can wear ankle socks and keep your legs bare. If it’s chilly, slip on a matching pair of tights with your dress!^{[2]
X
Research source}
- If you prefer skirts to dresses, try a flowing midi skirt and loose boho top with your Chelseas.
- Avoid wearing Chelsea boots with long dresses that cover up the shoes.
Advertisement
3
Go with black jeans and a neutral-colored sweater for an everyday vibe. Black Chelsea boots pair well with simple, solid earth tones like cream, burgundy, charcoal, and tan. These colors are also easy to mix-and-match! Grab your favorite solid-colored sweater and comfy black jeans for a look you can rock pretty much anywhere.^{[3]
X
Expert Source

Katie Quinn
Personal Wardrobe Stylist
Expert Interview. 14 April 2020.}
- Be sure to cuff the jeans or go with a pair that's slightly cropped so that your boots are fully visible.
- For example, wear black jeans with a dark gray sweater and black Chelsea boots. You could also try statement Chelseas, like leopard print, to jazz up your look a bit.^{[4]
  X
  Expert Source
  
  Katie Quinn
  Personal Wardrobe Stylist
  Expert Interview. 14 April 2020.}
- Throw on a knee-length tan coat or a black beanie to add another dimension to your look.^{[5]
  X
  Research source}
4
Create a fun, offbeat look by pairing denim overalls with your boots. For a cute, simple look, wear a plain white T-shirt under the denim overalls. Be sure to get denim overalls with a tapered leg and cuff them 2-3 times so that your calves show. Then, put on long, stripey socks so they'll be visible between the top of your boots and the cuffed legs to complete this quirky look.^{[6]
X
Research source}
- Medium wash denim works well for this, but you can definitely experiment with other washes.
- Wash refers to the color of the denim. Medium wash denim is a medium blue color that typically isn't faded at all. Light washes often look faded and range from light blue to almost white. Dark wash denim looks navy or almost black.^{[7]
  X
  Research source}

Method 2

Method 2 of 2:

Creating Dressier Looks

1
Pair black leather boots with a black turtleneck and dress pants. An all-black outfit instantly creates a more refined silhouette, so go with black dress pants and a black turtleneck to create a sleek look. Choose a slim-cut turtleneck sweater that falls just below the waistline.^{[8]
X
Research source}
- If you want to add some color, top off your outfit with a preppy plaid blazer or tweed coat.^{[9]
  X
  Research source}
- Don’t forget accessories, like black leather gloves, to complete this elegant look.
- If all-black isn’t your style, try tan dress pants with brown suede Chelsea boots and a light-colored sweater. Top it off with a matching blazer.
2
Wear statement Chelseas with high-waisted leather shorts for a night out. This is a great look for a party or a night on the town! Pair the high-waisted leather shorts with a matching camisole and loose, flowing kimono. Keep your legs bare and wear Chelsea boots in an eye-catching print, like snakeskin, or a bold color, like burgundy.^{[10]
X
Research source}
- For example, go for an all-black ensemble and wear a pair of red patent leather Chelseas for a cute pop of color.^{[11]
  X
  Research source}
3
Go with a pencil skirt and a long trench coat for timeless elegance. A trench coat in a neutral color, like tan, navy, or black, is easy to style with almost any outfit! If you’re headed to the office or an event, try a pencil skirt in a neutral color, like navy or black, with black Chelseas. Add a slim-fit, long-sleeved top and finish the look with the trench coat and a matching silk scarf.^{[12]
X
Research source}
- For a pop of color that still feels sophisticated, try wine-colored leather Chelsea boots with a tan trench coat and black pencil skirt.
4
Try cropped, wide-legged trousers with Chelseas for a work-ready outfit. This look is easy to throw together in the morning before heading to the office. Put on a cropped pair of dress trousers that have wide legs. Add a long-sleeved blouse in a complementary color. Add a matching pair of Chelsea boots to complete the look.^{[13]
X
Research source}
- Elevate the outfit by adding a slim-cut blazer and chunky knit scarf.
- Keep things simple by wearing solid, neutral colors.

Expert Q&A
Did you know you can get expert answers for this article? Unlock expert answers by supporting wikiHow

Question

What color of Chelsea boots do you think are the most versatile and why?

Katie Quinn
Image Consultant
Katie Quinn is an Image Consultant, Personal Wardrobe Stylist and the Founder of Q the Stylist, an image consulting service based in New York City helping men and women understand their specific goals, improve their wardrobe, performance, and life. She has over 11 years of image consulting experience and has worked as a stylist for Trunk Club, Modewalk, and Moda Operandi. Her work has been featured in Vogue, InStyle, Martha Stewart Weddings, Sheridan Road, Slate, Newsy, Rue, and Thrillist.

Katie Quinn

Image Consultant

Expert Answer

Support wikiHow by unlocking this expert answer.

Black Chelsea boots are the most versatile because the color works with dressier and casual outfits alike. Brown or tan is really only going to work with casual looks in the vast majority of cases.
Question

I'm in middle school but never get to wear my black Chelsea boots since I have gym every day. I never get a chance to wear them.

Community Answer

You can wear them at a party at school, with your neighborhood friend's birthday parties or while going shopping. During winters, you can wear them with your fancy or casual outfits, when you go for a walk or visiting relatives.